Synthesis and evaluation of novel hesperidin selenium-enriched derivatives as potential anti-inflammatory and antioxidant agents

Abstract

Hesperidin is a widely available and important flavonoid, but its insufficient activity has limited its application in the food and medicine industry. Therefore, we combined selenium with hesperidin according to the synergistic effect, selenylation modification of hesperidin was carried out through a thermal-assisted one-step reaction with selenium dioxide. Two products, 2′,3′-selenium-3,5-dihydroxy-4′-methoxy-7-rhamnoglucoside, 2′,3-selenium-3′,5-dihydroxy-4′-methoxy-7-rhamnoglucoside were obtained, with selenium contents of 120.60 ± 1.12 mg/g and 123.19 ± 1.54 mg/g, respectively. Structural elucidation revealed that the hesperidin was successfully introduced into selenium moiety, and produced C2[dbnd]C3 double bond, C3–OH reactive group in C-ring. The ability of hesperidin selenium-enriched derivatives to scavenge free radicals such as DPPH•, ABTS•+, and •OH was obviously higher than that of hesperidin, and they had a significant inhibitory effect on the LPS-induced inflammatory response in RAW264.7 cells. In this effort, the novel hesperidin selenium-enriched derivatives were successfully synthesized for the first time, which provides new ideas for the expanded application of hesperidin.